You probably did not identify his bragging because you agreed with him.
He bragged a lot about his past as a NG pilot, for example.
He also bragged about cutting taxes - all the while he did increase the budget (nominal, real and in %GDP) and create a deficit.
The "humble, nice guy one would like to drink a beer with (despite him being a dry alcoholic!) story is an obvious construction of an image. That's a creation of political advisors, sown by surrogates, PR stunts, books and partisan pundits.
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